419 E MACEWEN DRIVE, Osprey, FL 34229
OFF MARKET

419 E MACEWEN DRIVE
Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 4,201 sqft (on 0.72 acres)

$1,797,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $11,139/mo*
Refinance Your Home

$1,797,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $11,139/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,201 sqft
(on 0.72 acres)

Home Value

Trulia Estimate
$1.8M
Since last month
Decreased$24K (-1.3%)
Since last year
Increased$173K (+10.8%)
Since last sale
Increased$404K (+29.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +72% in the last 10 years
MonthEstimated value
2026
August 2026$1.78M
July 2026$1.78M
June 2026$1.8M
May 2026$1.79M
April 2026$1.75M
March 2026$1.74M
February 2026$1.72M
January 2026$1.69M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
898 MACEWEN DRIVE, Osprey, FL
0.27
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
402 WALLS WAY, Osprey, FL
0.31
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464
600 EAGLE WATCH LANE, Osprey, FL
0.10
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
264 SARATOGA COURT, Osprey, FL
0.20
Single-Family Home
$2,300,000
11/05/25
4
3.5
3,857
401 WALLS WAY, Osprey, FL
0.32
Single-Family Home
$1,700,000
07/17/26
4
3.5
4,387
453 E MACEWEN DRIVE, Osprey, FL
0.33
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
896 MACEWEN DRIVE, Osprey, FL
0.29
Single-Family Home
$2,300,000
04/06/26
4
5.5
4,858
434 MACEWEN DRIVE, Osprey, FL
0.18
Single-Family Home
$1,385,000
06/23/26
3
3
2,414
889 MACEWEN DRIVE, Osprey, FL
0.48
Single-Family Home
$2,100,000
01/30/26
4
4
3,235

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
425 E MACEWEN DRIVE, Osprey, FL 34229
0.08
$2,619,100
5
5.5
5,153
Off Market
600 EAGLE WATCH LANE, Osprey, FL 34229
0.10
$2,035,000
3
3
3,681
Recently Sold
588 EAGLE WATCH LANE, Osprey, FL 34229
0.10
$1,900,900
4
4.5
4,686
Off Market
627 EAGLE WATCH LANE, Osprey, FL 34229
0.16
$1,969,900
4
4.5
3,896
Off Market
639 EAGLE WATCH LANE, Osprey, FL 34229
0.18
$1,215,700
4
5.5
3,906
Off Market
434 MACEWEN DRIVE, Osprey, FL 34229
0.18
$1,385,000
3
3
2,414
Recently Sold
435 E MACEWEN DRIVE, Osprey, FL 34229
0.20
$1,812,400
4
3.5
4,087
Off Market
264 SARATOGA COURT, Osprey, FL 34229
0.20
$2,300,000
4
3.5
3,857
Recently Sold
402 MACEWEN DRIVE, Osprey, FL 34229
0.21
$1,589,800
3
3.5
3,565
Off Market
898 MACEWEN DRIVE, Osprey, FL 34229
0.27
$1,828,200
4
4
4,132
Off Market
916 MACEWEN DRIVE, Osprey, FL 34229
0.27
$1,900,000
5
7.5
5,986
For Sale

Local Information

  • Map ViewExplore the area around 419 E MACEWEN DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
0.72 acres
Living Area
4,201 sqft
Price/Sqft
$428
Parking
3 Car Garage
HOA
$133/Monthly

About this House

REDUCED $100,000 --NEW ROOF IS UNDER CONTRACT TO BE REPLACED.BEAUTIFUL CUSTOM-BUILT HOME situated at the end of a cul-de-sac on a Premium .72-acre golf course and lake homesite. This 4,201 SF of living space home has a 3-car side entry garage and offers many features that new homes today don't have. Imagine a home having four en-suite bedrooms for family and guests (two in a wing of their own), along with an office/den as well as three fireplaces located in the living room, the main bedroom and the family room. Features include a well-equipped, efficiently laid-out kitchen having premium custom built-in wood cabinets, a wall of them with glass fronts and lighted, and a wet bar; 12 foot and 10-foot ceilings with coffers and volume trays, crown molding and fans throughout. Entering the foyer, you have an expansive view, through a 16-foot window wall that pockets completely open, of the screened lanai having a large, sculpted, heated pool and spa, and an outdoor kitchen, all overlooking the quiet 'Heron' golf course and lake. Watch sunsets every evening of the year from the lanai or from a lakeside grove garden. The Oaks Club has many amenities, including two 18-hole championship golf courses, 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball courts, Fitness center, junior Olympic heated community pool plus the elegant CLUBHOUSE. Excellent location just a short distance to Gulf beaches, Legacy Hiking and Bike Trail, Pine View High School, Publix, Walmart, Lowes, Walgreen's/CVS and Target. Membership in The Oaks Club is mandatory. The owner has relocated; the home is presently vacant and can close any time.
419 E MACEWEN DRIVE, Osprey, FL 34229 is a 4 bedroom, 5 bathroom, 4,201 sqft single-family home built in 1997. It last sold for $1,375,000 on Sep 27, 2023 (5% below the $1,450,000 asking price). It is currently off market. The Trulia Estimate is $1,797,000, with a rent estimate of $6,820/month.

Home Details for 419 E MACEWEN DRIVE

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bathroom 3, Bathroom 4, Den, Dining Room, Family Room, Foyer, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4201 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Underground UtilitiesAppliances: Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, WasherDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Family Room, Living Room, Master BedroomSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: Outdoor Grill, Sliding DoorsFlooring: Ceramic Tile, Recycled/Composite Flooring
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Ceramic Tile, Recycled Composite Flooring
View
Has a ViewView: Golf Course, Water, Lake
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: Concrete TileExterior: Outdoor Grill, StorageFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Garage Door Opener,Garage Faces Side
Pool
Pool: Heated, In Ground, Lighting, Screen EnclosurePool
Frontage
WaterfrontWaterfront: Lake PrivilegesRoad Frontage: Street Dead-End, Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 177

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNot Attached PropertyNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Condition: CompletedParcel Number: 0141110002

Price & Status

Price
List Price: $1,450,000
Status Change & Dates
Off Market Date: Fri May 19 2023

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: OSPREYCommunity: OAKS 2 PH 3
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Laurel Nokomis MiddleHigh School: Venice Senior High

Building

Building Area
Building Area: 5913 Square Feet
Community rooms
Fitness Center

Community

Community Features: Buyer Approval Required, Deed Restrictions, Fitness Center, Golf Carts OK, Golf, Pool, RacquetballNot Senior Community

HOA

HOA Fee Includes: 24-Hour Guard, Common Area Taxes, Community Pool, ManagerHOA Name: Lighthouse ManagementHOA Phone: 941-460-5560Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $133/Monthly

Lot Information

Lot Area: 0.72 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4553067Water ViewWater View: Water, LakeShowing Considerations: No SignShowing Requirements: Go Direct, Lockbox - ElectronicUniversal Property Id: US-12115-N-0141110002-R-N

Additional Information

HOA Amenities: Clubhouse,Fitness Center,Gated,Golf Course,Pickleball Court(s),Pool,Racquetball,Recreation Facilities,Spa/Hot Tub,Tennis Court(s)
Last check for updates: about 10 hours ago
Listed by Ronald Stahl, (941) 374-1671
RON STAHL REALTY, (941) 374-1671
Bought with: Katheren Ayers, (941) 266-3193, AYERS AND ASSOCIATES REAL ESTATE, (941) 837-2778
Co-Buyer's Agent: Kelley Ann Ayers, (941) 544-7802, AYERS AND ASSOCIATES REAL ESTATE, (941) 837-2778
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4553067
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price and Tax history

DateEventPrice
Sep 27, 2023
Source: Stellar MLS #A4553067
Sold
$1,375,000
May 19, 2023
Source: Stellar MLS #A4553067
Pending
$1,450,000
May 17, 2023
Source: Stellar MLS #A4553067
PriceChange
$1,450,000
Price decreased by 14%
Mar 22, 2023
Source: Stellar MLS #A4553067
PriceChange
$1,695,000
Price decreased by 6%
Feb 22, 2023
Source: Stellar MLS #A4553067
PriceChange
$1,795,000
Price decreased by 5%

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM
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Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

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Homes for sale near 419 E MACEWEN DRIVE

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Off Market Homes Near 419 E MACEWEN DRIVE

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Frequently asked questions about 419 E MACEWEN DRIVE

  • What is 419 E MACEWEN DRIVE estimated to be worth?
    Trulia's estimated value for 419 E MACEWEN DRIVE in Osprey, FL is $1,797,000.
  • What is the price history for 419 E MACEWEN DRIVE?
    419 E MACEWEN DRIVE in Osprey, FL last sold for $1,375,000 in September 2023.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Osprey, FL.
  • Does 419 E MACEWEN DRIVE have air conditioning?
    Yes, 419 E MACEWEN DRIVE in Osprey, FL has air conditioning.
  • Does 419 E MACEWEN DRIVE have a pool?
    Yes, 419 E MACEWEN DRIVE in Osprey, FL has a pool.